US3310610A - Fluorotoluene-dithiol-phosphorodithioate - Google Patents
Fluorotoluene-dithiol-phosphorodithioate Download PDFInfo
- Publication number
- US3310610A US3310610A US368363A US36836364A US3310610A US 3310610 A US3310610 A US 3310610A US 368363 A US368363 A US 368363A US 36836364 A US36836364 A US 36836364A US 3310610 A US3310610 A US 3310610A
- Authority
- US
- United States
- Prior art keywords
- compound
- phosphorodithioate
- fluorotoluene
- dithiol
- employed
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 description 23
- 239000002917 insecticide Substances 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- 241000238876 Acari Species 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 230000005180 public health Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000256187 Anopheles albimanus Species 0.000 description 2
- 241000256113 Culicidae Species 0.000 description 2
- 241000255967 Helicoverpa zea Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 231100001225 mammalian toxicity Toxicity 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- LEWAHYJXJFHMKP-UHFFFAOYSA-N (4-fluorophenyl)methanedithiol Chemical compound FC1=CC=C(C(S)S)C=C1 LEWAHYJXJFHMKP-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000500891 Insecta Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000131095 Oniscidea Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 241001163248 Schoenocaulon officinale Species 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229940059904 light mineral oil Drugs 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- VSXGXPNADZQTGQ-UHFFFAOYSA-N oxirane;phenol Chemical compound C1CO1.OC1=CC=CC=C1 VSXGXPNADZQTGQ-UHFFFAOYSA-N 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1652—Polyol derivatives esterified at least twice by thiophosphoric acid groups
Definitions
- the compound of this invention being of a different structure and mode of action provides an alternate control agent for such resistant insects.
- Example I -Preparati0n of 4-fluor0t0luene-alpha,alphadithio bis(0,0-dimezhyl phosphorodithioate)
- 4-fluorobenzaldehyde containing one drop of concentrated sulfuric acid.
- the reaction mixture was heated to C. allowed to cool to room temperature, diluted with ether, washed 'with H 0 and dilute NaHCO and dried over MgSO filtered and then stripped.
- Example II bean plants were sprayed with suspensions of the test compound at varying concentrations and the L0 determined to be 0.00071%, by weight, in a similar manner to that described for the two spotted spider mite.
- the compound of this invention is an effective insecticide, the term insect including not only the members of the class Insecta, but also related or similar non-vertebrate animal organisms belonging to the allied classes of anthropods and including mites, ticks, spiders, wood lice, and the like.
- the compounds of this invention can be employed for insecticidal purposes by the use of any of the methods which are conventionally employed in that art.
- the compounds can either be sprayed or otherwise applied in the form of a solution or dispersion, or it can be absorbed on an inert, finely-divided solid and applied as a dust.
- Useful solutions for application by spraying, brushing, dipping, and the like, can be prepared by using These examples should not be 7 3 as the solvent any of the well-known inert horticultural carriers, including neutral hydrocarbons such as kerosene and other light mineral oil distillates of intermediate viscosity and volatility.
- Adjuvants such as spreading or wetting agents, can also be included in the solutions, representative materials of this character being fatty acid soaps, rosin salts, saponins, gelatin, casein, long-chain fatty alcohols, alkyl acid sulfonates, long chain alkyl sulfonates, phenol ethylene oxide condensates, ammonium salts, and the like.
- These solutions can be employed as such, or, more preferably, they can be dispersed or emulsified in water and the resulting aqueous dispersion or emulsion applied as a spray.
- Solid carrier materials which can be employed include talc, bentonite, lime gypsum, pyrophyllite and similar inert solid diluents. If desired, the compounds of the present invention can be employed as an aerosol, as by dispersing the same into the atmosphere by means of a compressed gas.
- concentration of the compound to be used with the above carriers is dependent upon many factors, including the carrier employed, the method and conditions of application, and the insect species to be controlled, a proper consideration and resolution of these factors being within the skill of those versed in the insecticide art.
- the compound of this invention is effective in concentrations of from about 0.01% to 0.5% based upon the total weight of the composition, though under some circumstances as little as about 0.00001% or as much as 2% or even more of the compound can be employed With good results from an insecticidal standpoint. Concentrates suitable for sale for dilution in the field may contain as much as 25-50% by weight, or even more, of the insecticide.
- the compound of this invention can be employed either as the sole toxic ingredient of the insecticidal composition or can be em ployed in conjunction with other insecticidally-active materials.
- Representative insecticides of this latter class include the naturally-occurring insecticides such as pyrethrum, rotenone, sabadilla, and the like, as well as the References Cited by the Examiner UNITED STATES PATENTS 2,754,242 7/1956 Kosolapoff 167-30 2,769,743 ll/ 1956 Mattson 167-30 3,155,707 11/1964 Kaver 260-461 3,157,686 11/1964 Pohlemann et a1. 260-461 CHARLES B. PARKER, Primary Examiner.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DENDAT1249583D DE1249583B (enrdf_load_stackoverflow) | 1964-05-18 | ||
| US368363A US3310610A (en) | 1964-05-18 | 1964-05-18 | Fluorotoluene-dithiol-phosphorodithioate |
| FR17285A FR1439364A (fr) | 1964-05-18 | 1965-05-17 | Insecticide organo-phosphoré contenant du fluor |
| CH683465A CH476460A (de) | 1964-05-18 | 1965-05-17 | Schädlingsbekämpfungsmittel, insbesondere insectizides und acarizides Mittel |
| GB20811/65A GB1041869A (en) | 1964-05-18 | 1965-05-17 | Fluorine-containing organophosphorus insecticides and miticides |
| BE664053D BE664053A (enrdf_load_stackoverflow) | 1964-05-18 | 1965-05-17 | |
| NL6506286A NL6506286A (enrdf_load_stackoverflow) | 1964-05-18 | 1965-05-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US368363A US3310610A (en) | 1964-05-18 | 1964-05-18 | Fluorotoluene-dithiol-phosphorodithioate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3310610A true US3310610A (en) | 1967-03-21 |
Family
ID=23450908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US368363A Expired - Lifetime US3310610A (en) | 1964-05-18 | 1964-05-18 | Fluorotoluene-dithiol-phosphorodithioate |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3310610A (enrdf_load_stackoverflow) |
| BE (1) | BE664053A (enrdf_load_stackoverflow) |
| CH (1) | CH476460A (enrdf_load_stackoverflow) |
| DE (1) | DE1249583B (enrdf_load_stackoverflow) |
| FR (1) | FR1439364A (enrdf_load_stackoverflow) |
| GB (1) | GB1041869A (enrdf_load_stackoverflow) |
| NL (1) | NL6506286A (enrdf_load_stackoverflow) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2754242A (en) * | 1953-03-11 | 1956-07-10 | Monsanto Chemicals | Process of combatting insects utilizing phosphinates |
| US2769743A (en) * | 1952-04-18 | 1956-11-06 | Union Oil Co | Pest control utilizing pesticidal compositions of phosphorus |
| US3155707A (en) * | 1961-08-02 | 1964-11-03 | Dow Chemical Co | Symmetrical diaryl diamidodithiopyrophosphates |
| US3157686A (en) * | 1961-12-23 | 1964-11-17 | Basf Ag | Diol esters of dithiophosphorylacetic acids and process for their production |
-
0
- DE DENDAT1249583D patent/DE1249583B/de active Pending
-
1964
- 1964-05-18 US US368363A patent/US3310610A/en not_active Expired - Lifetime
-
1965
- 1965-05-17 FR FR17285A patent/FR1439364A/fr not_active Expired
- 1965-05-17 BE BE664053D patent/BE664053A/xx unknown
- 1965-05-17 GB GB20811/65A patent/GB1041869A/en not_active Expired
- 1965-05-17 CH CH683465A patent/CH476460A/de not_active IP Right Cessation
- 1965-05-18 NL NL6506286A patent/NL6506286A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2769743A (en) * | 1952-04-18 | 1956-11-06 | Union Oil Co | Pest control utilizing pesticidal compositions of phosphorus |
| US2754242A (en) * | 1953-03-11 | 1956-07-10 | Monsanto Chemicals | Process of combatting insects utilizing phosphinates |
| US3155707A (en) * | 1961-08-02 | 1964-11-03 | Dow Chemical Co | Symmetrical diaryl diamidodithiopyrophosphates |
| US3157686A (en) * | 1961-12-23 | 1964-11-17 | Basf Ag | Diol esters of dithiophosphorylacetic acids and process for their production |
Also Published As
| Publication number | Publication date |
|---|---|
| BE664053A (enrdf_load_stackoverflow) | 1965-11-17 |
| GB1041869A (en) | 1966-09-07 |
| FR1439364A (fr) | 1966-05-20 |
| NL6506286A (enrdf_load_stackoverflow) | 1965-11-18 |
| CH476460A (de) | 1969-08-15 |
| DE1249583B (enrdf_load_stackoverflow) |
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